A Brief History of Drake and 21 Savage Collaborations (2024)

Last weekend, Drake and 21 Savage announced their joint project Her Loss, set to be released this Friday. The title hints that the album might lean more into Drake’s lovelorn wheelhouse than 21 Savage’s steely menace, and finds two of the rap world’s biggest artists expanding their musical synergy for a full-length release.

“Jimmy Cooks,” from Drake’s Honestly, Nevermind, “Knife Talk” from Certified Lover Boy, and “Sneakin” are three well-regarded tracks in Drake’s canon, while “Mr Right Now” is a more polarizing offering from 21 and Metro-Boomin’s Savage Mode II project. 21 has compared the two to a modern day “Kobe-Shaq” pairing on the mic, even after he previously told Akademiks that “if I wasn’t a rapper, I don’t feel like I still would listen to Drake, for real.”

Stil, “Drake just a genuine-ass good-hearted person,” Savage has said about the Toronto artist. “‘He did a lot of sh*t he didn’t have to do. He do a lot of sh*t for up-and-coming rappers, period. I don’t think he get his respect for that. Every f*ckin’ year, he pull a new artist up. Ain’t no other artist on his level do that sh*t.”

The two share October birthdays and together have more hits than misses. They also aren’t strangers to collaborating with other artists on double albums. Drake released What A Time To Be Alive with Future in 2015, his trap-driven victory lap after releasing If You’re Reading This It’s Too Late and besting Meek Mill in their highly publicized beef earlier that year. Drake is such a versatile, prolific artist that he’s stoked an impressive creative bond with a range of MCs over the years. Rumors of Drake-Rick Ross and Drake-LIl Wayne projects have festered at different times of his career based on their bevy of classic collaborations. But Her Loss is his official WATTBA collab album followup.

21 Savage dropped Without Warning with Offset and Metro-Boomin in 2017, a 10-track ATL affair where the two MCs were equally gruff and braggadocious over murky Metro production. 21 Savage and Metro-Boomin’s Savage Mode projects have also been billed as collaboration projects, though they’re moreso rapper-producer albums. Her Loss is Drake and 21’s first collaboration project in seven and five years, respectively, a time period in which 21 Savage has reached the cusp of rap superstardom, while Drake’s hold on pop music has remained firm, even as albums like 2018’s Scorpion, 2020’s Dark Lane Demo Tapes, and 2021’s Certified Lover Boy have detractors who’ve deemed them fan service projects because of their tendency to offer each sect of Drake’s audience two to three songs: there’s R&B Drake, “mob boss” Drake, Afrobeats Drake, and reflective “5PM” Drake in equal proportion. That’s why his foray into dance music Honestly, Nevermind, from earlier this year, was refreshing, and why this follow-up is poised to be another strategic success.

More than a financially-driven partnership, however, Drake and 21 share a bond forged in friendship. According to 21’s manager Meezy, they’ve never had to discuss money over any collaborations. During a 2022 Clubhouse session, Meezy revealed that 21 rarely does paperwork with artists he sparks genuine friendship with. “A lot of the artists, they are low-key peers,” Meezy said. “So sh*t just be happening naturally. A nigg* might be in the studio, somebody ask, ‘Ay, can you do this song?’ And it happens, because nigg*s f*ck with each other, so you ain’t gonna talk about money.” Now that the two established stars are set to commemorate their creative chemistry in grand fashion, we put together a brief snippet of Drake and 21 Savage’s most memorable moments.

“Sneakin”

In 2016, Drake and 21 Savage released their first collaboration, a week after 21’s birthday. That night, Drake dropped “Sneakin” alongside “Fake Love” and “Two Birds, One Stone.” The 21-assisted “Sneakin” sounds like a fur-clad Drake rapping at the peak of his post-Meek Mill reverie. Over production courtesy of London On The Track, Drake raps to a mystery foe: “’bout to take over your city and you can’t stand it / My accountant say you sinking like the Titanic.” His album Views was on its way to becoming the most-streamed record (based on album-equivalent units) of the year, so he could’ve been talking to anyone from his commercial steeple. But he wasn’t referring to 21, who follows off Drake’s boasts with his own verse, where he glides over London’s 808s and lets listeners know, “We the ones poppin’, We the ones shoppin’ / We the ones droppin’, N—-s we the ones.” In “Sneakin’s” Gab3-directed visual, the two look every bit of “the ones” while partying in a grotto with frolicking women.

“Knife Talk” and “Mr Right Now”

You know a duo trusts each other when they start trying to alternate each other’s roles. On “Mr. Right Now,” from 21 Savage and Metro Boomin’s Savage Mode II project, 21 decided to take over hook duties from Drake, who has the longest verse on the song. 21 has likened his work with Drake to Shaq and Kobe, though it would be a confusing decision if Shaq had decided to bring the ball up and pass to Kobe in the post for an entire game. The two repeated the dynamic on “Knife Talk,” which is a decidedly grim track for a project deemed Certified Lover Boy. After a short Project Pat verse, 21 starts the song off, trading verses with Drake, and once again taking on the hook, sounding more at home as he lets the listener know, that “Gang sh*t, that’s all I’m on.”

“Jimmy Cooks”

21 Savage was the only feature on Drake’s otherwise dance-focused album, Honestly Nevermind, and he showed up on the most overtly rap-leaning track on the project. Drake starts “Jimmy Cooks” in typically braggadocios form, rapping over an idyllic sample before, inspired by the previous dance compositions, things take an abrupt shift, and the two pass the baton on a single line. “If I let my nigg* 21 tell it, you a puss*yyy,” Drake raps. 21 hangs on to the last word, then jolts the album with his extended verse, threatening to “smack the backside of his head like he Bart” and affirming, “I got mad love for the boy, yeah, that’s my twizzin.” The Mahfuz Sultan-directed video shows the two in front of a giant green screen displaying different images, but it stops in the middle of Drake’s verse to announce Her Loss, then shows the two leisurely talking for the rest of the video. Who knows what they were discussing that took precedence over the rest of the song, but It’s their world, we’re just living in it.

Birthday Ferraris

The “Jimmy Cooks” video dropped on 21 Savage’s 30th birthday, but that isn’t the first time the two made headlines on 21’s earthstrong. In 2016, Drake called the Atlanta rapper “a young October king with all the juice right now,” then put his money where his thoughts were by renting 21 a Ferrari to cruise around LA. When 21 first posted a picture of him with the car and captioned it “bday gift from @champagnpapi,” many assumed that Drake had outright purchased the car. But 21 later clarified that it was just a rental. “Nah, he ain’t buy me no car … He did some real sh*t,” 21 Savage told radio station Real 92.3. “We was just talking, and I was like ‘Man, I want a Ferrari or some sh*t.’ So, he just got me one for the whole time I was in L.A. for my birthday. But I fell in love with the car, so I just went and bought one. He looked out.” He also told GQ that it was the only gift he got that year. And now the two are set to come together and give the rap world a gift during both of their birth month.